Chapter 22: Problem 40
Draw all the structural and geometrical (cis-trans) isomers of bromochloropropene.
Chapter 22: Problem 40
Draw all the structural and geometrical (cis-trans) isomers of bromochloropropene.
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Get started for freeCis-trans isomerism is also possible in molecules with rings. Draw the cis and trans isomers of 1,2 -dimethylcyclohexane. In Exercise 41, you drew all of the noncyclic structural and geometric isomers of \(\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{~F}\). Now draw the cyclic structural and geometric isomers of \(\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{~F}\).
Consider the following reactions. For parts \(\mathrm{b}-\mathrm{d}\), see Exercise \(62 .\) a. When \(\mathrm{C}_{5} \mathrm{H}_{12}\) is reacted with \(\mathrm{Cl}_{2}(g)\) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of \(\mathrm{C}_{5} \mathrm{H}_{12}\) in this reaction? b. When \(\mathrm{C}_{4} \mathrm{H}_{8}\) is reacted with \(\mathrm{H}_{2} \mathrm{O}\), a tertiary alcohol is produced as the major product. What is the structure of \(\mathrm{C}_{4} \mathrm{H}_{8}\) in this reaction? c. When \(\mathrm{C}_{7} \mathrm{H}_{12}\) is reacted with \(\mathrm{HCl}\), 1 -chloro-1-methylcyclohexane is produced as the major product. What are the two possible structures for \(\mathrm{C}_{7} \mathrm{H}_{12}\) in this reaction? d. When a hydrocarbon is reacted with \(\mathrm{H}_{2} \mathrm{O}\) and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? e. When \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) is oxidized, a carboxylic acid is produced. What are the possible structures for \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) in this reaction?
Draw the structures of the two dipeptides that can be formed from serine and alanine.
In glycine, the carboxylic acid group has \(K_{\mathrm{a}}=4.3 \times 10^{-3}\) and the amino group has \(K_{\mathrm{b}}=6.0 \times 10^{-5}\). Use these equilibrium constant values to calculate the equilibrium constants for the following. a. \({ }^{+} \mathrm{H}_{3} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}+\mathrm{H}_{2} \mathrm{O} \rightleftharpoons \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}+\mathrm{H}_{3} \mathrm{O}^{+}\) b. \(\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}+\mathrm{H}_{2} \mathrm{O} \rightleftharpoons \mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2} \mathrm{H}+\mathrm{OH}^{-}\) c. \({ }^{+} \mathrm{H}_{3} \mathrm{NCH}_{2} \mathrm{CO}_{2} \mathrm{H} \rightleftharpoons 2 \mathrm{H}^{+}+\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CO}_{2}^{-}\)
Reagents such as \(\mathrm{HCl}, \mathrm{HBr}\), and
\(\mathrm{HOH}\left(\mathrm{H}_{2} \mathrm{O}\right)\) can add across carbon-
carbon double and triple bonds, with \(\mathrm{H}\) forming a bond to one of the
carbon atoms in the multiple bond and \(\mathrm{Cl}, \mathrm{Br}\), or OH
forming a bond to the other carbon atom in the multiple bond. In some cases,
two products are possible. For the major organic product, the addition occurs
so that the hydrogen atom in the reagent attaches to the carbon atom in the
multiple bond that already has the greater number of hydrogen atoms bonded to
it. With this rule in mind, draw the structure of the major product in each of
the following reactions.
a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{H}_{2}
\mathrm{O} \stackrel{\mathrm{H}^{*}}{\longrightarrow}\)
b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{HBr}
\longrightarrow\)
c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}+2
\mathrm{HBr} \longrightarrow\)
d.
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